Boosting the activity of Mizoroki-Heck cross-coupling reactions with a supramolecular palladium catalyst favoring remote Zn…pyridine interactions - Archive ouverte HAL Access content directly
Journal Articles Faraday Discussions Year : 2023

Boosting the activity of Mizoroki-Heck cross-coupling reactions with a supramolecular palladium catalyst favoring remote Zn…pyridine interactions

Abstract

Transition metal catalysis benefitting from supramolecular interactions in the secondary coordination sphere in order to pre-organize substrates around the active site and reach a specific selectivity typically occur under long reaction times and mild reaction temperatures with the aim to maximize such subtle effects. Herein, we demonstrate that the kinetically labile Zn···N interaction between a pyridine substrate and a zinc-porphyrin site serving for substrate binding is a unique type of non-covalent interaction that enables to identify supramolecular effects in transition metal catalysis after one hour at a high reaction temperature of 130 oC. Under carefully selected reaction conditions, supramolecularly-regulated palladium-catalyzed Mizoroki-Heck reactions between 3-bromopyridine and terminal olefins (acrylates or styrenes) proceeded in a more efficient manner compared to the non-supramolecular version. The supramolecular catalysis developed here displayed also interesting substrate-selectivity patterns.
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Dates and versions

hal-03932107 , version 1 (10-01-2023)

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Naba Abuhafez, Rafael Gramage-Doria. Boosting the activity of Mizoroki-Heck cross-coupling reactions with a supramolecular palladium catalyst favoring remote Zn…pyridine interactions. Faraday Discussions, 2023, ⟨10.1039/D2FD00165A⟩. ⟨hal-03932107⟩
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